Hi @Sean Kuchle ,
I want to check with you that your default view contains all the documents in the entire library? Check that the default view may have been modified. As for what you mentioned, 4 documents are displayed without pressing enter, because the given suggestion document is searched from the full library, no matter which view, the search box is displayed under the same. If the desired result appears after enter, there is a high probability that there are no files in the default view that contain the search.
According to your description, your need is to search for the required files throughout the library, and the SP's search is for the current view, so make sure the default view for the search is complete.
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